Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature

To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to b...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Kim, Soeun [verfasserIn] Hong, Jun Ui [verfasserIn] Ha, Miran [verfasserIn] Noh, Seung Man [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2021

Schlagwörter:	Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing

Übergeordnetes Werk:	Enthalten in: Progress in organic coatings - Amsterdam [u.a.] : Elsevier Science, 1972, 161
Übergeordnetes Werk:	volume:161

DOI / URN:	10.1016/j.porgcoat.2021.106501

Katalog-ID:	ELV006825281

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520			\|a To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials.
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Indexfelder

author_variant	s k sk j u h ju juh m h mh s m n sm smn
matchkey_str	kimsoeunhongjunuihamirannohseungman:2021----:ulualioyntcosiknaetbokdyehcyaeucinlzdyao
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publishDate	2021
allfields	10.1016/j.porgcoat.2021.106501 doi (DE-627)ELV006825281 (ELSEVIER)S0300-9440(21)00372-6 DE-627 ger DE-627 rda eng 540 DE-600 52.78 bkl Kim, Soeun verfasserin aut Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials. Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing Hong, Jun Ui verfasserin aut Ha, Miran verfasserin aut Noh, Seung Man verfasserin aut Enthalten in Progress in organic coatings Amsterdam [u.a.] : Elsevier Science, 1972 161 Online-Ressource (DE-627)320530647 (DE-600)2015714-9 (DE-576)25948492X nnns volume:161 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 52.78 Oberflächentechnik Wärmebehandlung AR 161
spelling	10.1016/j.porgcoat.2021.106501 doi (DE-627)ELV006825281 (ELSEVIER)S0300-9440(21)00372-6 DE-627 ger DE-627 rda eng 540 DE-600 52.78 bkl Kim, Soeun verfasserin aut Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials. Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing Hong, Jun Ui verfasserin aut Ha, Miran verfasserin aut Noh, Seung Man verfasserin aut Enthalten in Progress in organic coatings Amsterdam [u.a.] : Elsevier Science, 1972 161 Online-Ressource (DE-627)320530647 (DE-600)2015714-9 (DE-576)25948492X nnns volume:161 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 52.78 Oberflächentechnik Wärmebehandlung AR 161
allfields_unstemmed	10.1016/j.porgcoat.2021.106501 doi (DE-627)ELV006825281 (ELSEVIER)S0300-9440(21)00372-6 DE-627 ger DE-627 rda eng 540 DE-600 52.78 bkl Kim, Soeun verfasserin aut Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials. Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing Hong, Jun Ui verfasserin aut Ha, Miran verfasserin aut Noh, Seung Man verfasserin aut Enthalten in Progress in organic coatings Amsterdam [u.a.] : Elsevier Science, 1972 161 Online-Ressource (DE-627)320530647 (DE-600)2015714-9 (DE-576)25948492X nnns volume:161 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 52.78 Oberflächentechnik Wärmebehandlung AR 161
allfieldsGer	10.1016/j.porgcoat.2021.106501 doi (DE-627)ELV006825281 (ELSEVIER)S0300-9440(21)00372-6 DE-627 ger DE-627 rda eng 540 DE-600 52.78 bkl Kim, Soeun verfasserin aut Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials. Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing Hong, Jun Ui verfasserin aut Ha, Miran verfasserin aut Noh, Seung Man verfasserin aut Enthalten in Progress in organic coatings Amsterdam [u.a.] : Elsevier Science, 1972 161 Online-Ressource (DE-627)320530647 (DE-600)2015714-9 (DE-576)25948492X nnns volume:161 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 52.78 Oberflächentechnik Wärmebehandlung AR 161
allfieldsSound	10.1016/j.porgcoat.2021.106501 doi (DE-627)ELV006825281 (ELSEVIER)S0300-9440(21)00372-6 DE-627 ger DE-627 rda eng 540 DE-600 52.78 bkl Kim, Soeun verfasserin aut Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials. Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing Hong, Jun Ui verfasserin aut Ha, Miran verfasserin aut Noh, Seung Man verfasserin aut Enthalten in Progress in organic coatings Amsterdam [u.a.] : Elsevier Science, 1972 161 Online-Ressource (DE-627)320530647 (DE-600)2015714-9 (DE-576)25948492X nnns volume:161 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 52.78 Oberflächentechnik Wärmebehandlung AR 161
language	English
source	Enthalten in Progress in organic coatings 161 volume:161
sourceStr	Enthalten in Progress in organic coatings 161 volume:161
format_phy_str_mv	Article
bklname	Oberflächentechnik Wärmebehandlung
institution	findex.gbv.de
topic_facet	Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing
dewey-raw	540
isfreeaccess_bool	false
container_title	Progress in organic coatings
authorswithroles_txt_mv	Kim, Soeun @@aut@@ Hong, Jun Ui @@aut@@ Ha, Miran @@aut@@ Noh, Seung Man @@aut@@
publishDateDaySort_date	2021-01-01T00:00:00Z
hierarchy_top_id	320530647
dewey-sort	3540
id	ELV006825281
language_de	englisch
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author	Kim, Soeun
spellingShingle	Kim, Soeun ddc 540 bkl 52.78 misc Pyrazole misc Dual-curable crosslinking misc Polyurethane misc Automotive clearcoat misc Low-temperature thermal curing Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
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topic_title	540 DE-600 52.78 bkl Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature Pyrazole Dual-curable crosslinking Polyurethane Automotive clearcoat Low-temperature thermal curing
topic	ddc 540 bkl 52.78 misc Pyrazole misc Dual-curable crosslinking misc Polyurethane misc Automotive clearcoat misc Low-temperature thermal curing
topic_unstemmed	ddc 540 bkl 52.78 misc Pyrazole misc Dual-curable crosslinking misc Polyurethane misc Automotive clearcoat misc Low-temperature thermal curing
topic_browse	ddc 540 bkl 52.78 misc Pyrazole misc Dual-curable crosslinking misc Polyurethane misc Automotive clearcoat misc Low-temperature thermal curing
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title	Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
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title_full	Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
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author_browse	Kim, Soeun Hong, Jun Ui Ha, Miran Noh, Seung Man
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author-letter	Kim, Soeun
doi_str_mv	10.1016/j.porgcoat.2021.106501
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title_sort	dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
title_auth	Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
abstract	To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials.
abstractGer	To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials.
abstract_unstemmed	To develop a polyurethane-based automotive clearcoat with a lower curing temperature, methacrylate-functionalized pyrazole derivatives were newly designed and synthesized as isocyanate blocking agents and their chemical structures were identified by 1H NMR. These novel blocking agents were used to block the functional groups of hexamethylene diisocyanate (HDI) trimer (commercially known as Desmodur N3300), and density functional theory simulations were performed to predict the activation energy of the deblocking process and to determine the HN distance in the pyrazole molecules. The curing behavior of the blocked isocyanate with polyol resin at 110, 120, and 130 °C was investigated using an oscillatory rheometer and a rigid-body pendulum tester. In addition, their results were compared with those for a commercially available 3,5-dimethyl pyrazole-blocked HDI trimer (Desmodur PL350). The thermal properties of the clearcoat films cured at 130 °C were investigated using thermogravimetric analysis, differential scanning calorimetry, and dynamic mechanical analysis, and the surface mechanical properties of the cured films were evaluated using a nano-indentation tester. The novel pyrazole blocking agents contributed to lowering the deblocking temperature and enhancing the mechanical properties via supplementary radical polymerization of deblocked methacrylate-functionalized pyrazoles, resulting in interpenetrating crosslinked polymer networks. This study provides a new concept of isocyanate blocking agents with lower deblocking temperatures and higher crosslinking densities, resulting in blocked isocyanates that can be used in various coating materials.
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title_short	Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature
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author2	Hong, Jun Ui Ha, Miran Noh, Seung Man
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doi_str	10.1016/j.porgcoat.2021.106501
up_date	2024-07-06T22:40:36.501Z
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Dual-curable isocyanate crosslinking agents blocked by methacrylate-functionalized pyrazoles with lower curing temperature

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